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A rare photo of Vince McMahon out in the world

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Apparently the Chairman is a big Dave Chappelle fan.

Donnell Rawlings’ Instagram

We don’t see much of Vincent Kennedy McMahon these days.

He only rarely shows up on Raw, SmackDown, or PPV; former SmackDown Executive Director Eric Bischoff believes its because “there was some awareness from Vince’s part that his time on television as a character was in his rear view mirror.” In 2021, McMahon is more likely to show up as a talking head on a WWE documentary than as “Mr. McMahon” on one of his pro wrestling sports entertainment programs.

VKM’s never been paparazzi bait. Partly that’s because he doesn’t travel in such a way that he can be ambushed in airport parking lots for TMZ interviews. But it’s also because he’s famously such a workaholic he hadn’t heard of Scarface when Scott Hall pitched a character loosely based on Al Pacino’s famous lead character, Tony Montana... almost a decade after Brian DePalma’s film premiered.

All of that is why it’s pretty shocking to see this Instagram post from comedian Donnell Rawlings. Not only does it capture Vince outside the workplace, it shows him partaking in a pop culture event like the tour Dave Chappelle is currently headlining with his old pal Rawlings & other stand-ups.

The 75 year old McMahon looked like he had a pretty great time at the Chappelle & Friends show Saturday night (June 26) at Foxwoods Casino in Mashantucket, Connecticut - if you know what I mean.

Sadly, I can not confirm if Vince and Dave smoked together. Or if the WWE Chairman and Rawlings took turns screaming this at each other.

Cool pic, though.